Multifunctional surfactant and preparation method therefor

ABSTRACT

The present disclosure relates to a polymerizable surfactant with reducibility and a preparation method thereof. The acid anhydride is reacted with a long-chain fatty alcohol to obtain an intermediate of an anhydride monoester, and then the obtained intermediate is reacted with the hydrochloride of dimethylaminohalogenated alkane, and a polymerizable surfactant with reducibility is obtained by post-processing. The polymerizable surfactant can not only play a role as a reactive emulsifier and copolymerize with monomers to obtain a soap-free emulsion, but also form a redox initiation system with peroxide, and conduct redox emulsion polymerization at room temperature. The soap-free emulsion synthesized by the polymerizable surfactant synthesized can greatly reduce the energy consumption in production, and can carry out one-step emulsion polymerization at normal temperature or low temperature to obtain an environment-friendly emulsion with a branched structure, thereby obtaining coatings with excellent water resistance, weather resistance, and impact resistance.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation of U.S. patent application Ser. No. 17/936,932, filed on Sep. 30, 2022, which is a continuation of International Application No. PCT/CN2020/140467, filed on Dec. 29, 2020, which claims priority of Chinese Patent Application No. 202010242562.2 filed on Mar. 31, 2020, the contents of which are incorporated herein by reference to their entirety.

TECHNICAL FIELD

The present disclosure is a fine chemical technology field, in particular, to a polymerizable surfactant with reducibility and a preparation method thereof.

BACKGROUND

In addition to a hydrophilic group and a lipophilic group, a polymerizable surfactant also includes a reactive functional group. The reactive functional group may participate in emulsion polymerization. While playing a role of a conventional emulsifier, the reactive functional group is also bonded to the surface of polymer particles in a covalent manner to become a part of the polymer, avoiding desorption of the emulsifiers from the polymer particles or migration of the emulsifiers in an emulsion film, thereby improving the stability of the emulsion and improving the performance of the emulsion film.

Since the application of a polymerizable emulsifier for polymerization in 1956 by Bistline, a large number of polymerizable emulsifiers have been synthesized and applied to various aspects, and various materials with excellent performance have been obtained. The existing polymerizable surfactant is a series of polymerizable surfactants including different reaction groups (acrylate, styrene, maleic anhydride, etc.) and different ionic characteristics (cation, anion, non-ion, etc.). Because a soap-free emulsion system does not contain emulsifiers, the soap-free emulsion system has many excellent performance. However, due to the lack of the protective effect of the emulsifiers, the stability of the emulsion decreases and the solid content is relatively low. Therefore, developing a new type of reactive surfactant is a primary problem in soap-free emulsion polymerization.

A redox initiation system forms radical reactive species via inner sphere electron transfer (ISET), thereby initiating the polymerization of vinyl monomers. In the 1930s and 1940s, scientists of Germany, the United States, and Britain have discovered that the redox initiation system can not only shorten the induction period, but also increase the polymerization rate. Compared with the single initiator in the general thermal decomposition, the chain initiation activation energy of the redox initiation system is about 40 to 60 kJ/mol, which can reduce the polymerization temperature and even cause the polymerization to be carried out at or lower than the room temperature.

The redox initiation system initiates the polymerization quickly, and can initiate the polymerization at a lower temperature, and the obtained polymer has a high molecular weight. However, as a kind of emulsion polymerization, because a large amount of emulsifier is added, the redox initiation system also has the shortcomings of insufficient film-forming properties and mechanical properties of the emulsion.

At present, the molecular weight and solid content of environmental protection coatings are low, which cannot meet the increasingly strict regulations and construction requirements. The preparation of emulsion coatings requires a large amount of emulsifier to maintain the stability of the system, and the water resistance and mechanical properties of the coatings after emulsion film formation are poor, limiting the development and application of the environmental protection coatings.

SUMMARY

The purpose of the present invention is to introduce a tertiary amine group with reducibility into one end of acid anhydride. Because the tertiary amine has a certain hydrophilic property, the tertiary amine is used as the hydrophilic end of the polymerizable surfactant, and the other end of the acid anhydride is connected with a long carbon chain as the lipophilic end. As a result, the polymerizable surfactant with reducibility is obtained with one end being hydrophilic and the other end being lipophilic. The surfactant provided by the present disclosure uses acid anhydride, long-chain fatty alcohol, and hydrochloride of dimethylaminohaloalkane as main raw materials, and the prepared polymerizable surfactant has excellent emulsifying performance and can also be used as a reducing agent in a redox initiation reaction. One-step emulsion polymerization can be carried out at room temperature or low temperature to obtain an environmentally friendly emulsion with a branched structure, and then a coating with excellent water resistance, weather resistance, and impact resistance can be obtained.

The general structural formula of the polymerizable surfactant with reducibility provided by the present disclosure is represented as:

wherein a long-chain alkyl R₁ is —C₁₂H₂₅, —C₁₄H₂₉, or —C₁₆H₃₃, and a long-chain alkyl R₂ is —C₂H₄—, —C₃H₆—, or —C(CH₃) CH₂—.

The present disclosure also provides a preparation method for polymerizable surfactants with reducibility. An intermediate of anhydride monoester is obtained by reacting an anhydride with long-chain fatty alcohol. The obtained intermediate reacts with hydrochloride of dimethylaminohaloalkane. The polymerizable surfactant with reducibility is obtained through a post-treatment.

The specific operations of the preparation method of polymerizable surfactants includes:

-   -   (1) preparation of an intermediate product, including: mixing         the anhydride and the long-chain fatty alcohol; heating the         mixture of the anhydride and the long-chain fatty alcohol to a         molten state at 80° C.; stirring the molten mixture for 1 h;         adding heptane to the molten mixture; stirring the molten         mixture to form a uniform solution; stirring and cooling the         solution to room temperature; placing the solution for 3 h;         stirring and cooling the solution to 15° C.; placing the         solution for 2 h; collecting a precipitate; recrystallizing the         precipitate with heptane for 2-3 times; obtaining a solid by         filtration; washing the solid with water for 2-3 times; and         obtaining the intermediate monoester by freeze drying; wherein,         the acidic anhydride is Malay acid anhydride or itaconic         anhydride; the long-chain fatty alcohol is dodecanol,         tetradecanol, or hexadecanol;     -   (2) preparation of the reducible polymerizable surfactant,         including: dissolving the intermediate monoester of         operation (1) in chloroform; adding an aqueous solution of         potassium carbonate and 18-crown-6 drop by drop to the         intermediate anhydride monoester chloroform solution at room         temperature; stirring the chloroform solution at 50-60° C. for         0.4 h; and obtaining a reaction solution by adding a         hydrochloric acid brine solution of dimethylaminohaloalkane drop         by drop to the chloroform solution for reaction at 50° C. for         15-20 h; wherein, the hydrochloride salt of the         dimethylaminohaloalkane is 2-dimethylaminochloroethane         hydrochloride, 3-(N, N-dimethyl) amino-1-chloropropane         hydrochloride or 3-dimethylamino-2-methyl-1-chloropropane         hydrochloride; an amount-of-substance ratio-of the anhydride and         the long chain fatty alcohol in operation (1) is 1:1 to 1.1; and     -   (3) the post treatment, including: cooling the reaction solution         obtained in operation (2) to room temperature; separating each         layer of the reaction solution; adding the separated chloroform         solution to anhydrous sodium sulfate for drying overnight;         passing the chloroform solution through an alkaline alumina         column; removing the chloroform at 30-40° C. with a rotary         evaporator; performing vacuum dry overnight at 30° C. with a         vacuum of 2-3 kpa, wherein a resulting product is the         polymerizable surfactant with reducibility.

The present disclosure has the following advantages:

-   -   1. The present disclosure uses a synthesis method to prepare a         polymerization surfactant with reducibility, and the prepared         surfactant has excellent emulsification performance.     -   2. The synthetic surfactant, along with an oxidizing agent, can         form a redox initiation system, and can carry out soap-free         emulsion polymerization at room temperature or even low         temperature without adding additional reducing agent, which can         greatly reduce the energy consumption of production.     -   3. The surfactant of the present invention has the properties of         a monomer with reducibility, and can obtain an emulsion with a         branched structure, thereby obtaining a coating with excellent         water resistance, weather resistance and impact resistance.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is an exemplary nuclear magnetic resonance (NMR) image of 2-(dimethylamino) ethyl maleate dodecyl ester in embodiment 1;

FIG. 2 is an exemplary NMR image of itaconic acid 2-(dimethylamino)ethyl dodecyl; and

FIG. 3 is an exemplary molecular weight distribution curve of a branched polymer obtained in the embodiment 7.

DETAILED DESCRIPTION

The present disclosure uses the following examples to further explain the technical characteristics of the present disclosure, but the protection scope of the present disclosure is not limited to the following examples.

Embodiment 1

-   -   (1) Preparation of an intermediate. 4.90 g (0.05 mol) maleic         anhydride and 10.25 g (0.055 mol) lauryl alcohol were stirred at         80° C. for 1 h at the molten state. 15 ml heptane was added to         the molten mixture. The molten mixture was stirred to form a         uniform solution. The solution was placed at room temperature         for 3 h with stirring, and placed at 15° C. for 2 h with         stirring. A precipitate was collected. The precipitate was         recrystallized with heptane for 2-3 times. A solid was obtained         by filtration. The solid was washed with water for 2-3 times.         The intermediate of anhydride monoester was obtained by freeze         drying overnight. The yield may reach 92.8%.     -   (2) Preparation of the polymerizable surfactant with         reducibility. 11.36 g (0.04 mol) monododecyl maleate was         dissolved in 100 ml chloroform. A water solution of 11.06 g         (0.08 mol) potassium carbonate and 1.05 g (0.004 mol) 18-crown-6         was added dropwise to the chloroform solution at room         temperature, and the mixture was stirred at 60° C. for 0.4 h. A         water solution of 5.76 g (0.04 mol) 2-dimethylamino chloroethane         hydrochloride (Aladdin, CAS: 4584-46-7) was added dropwise to         the above water-chloroform solution, for reaction at 50° C. for         20 h.     -   (3)The post-treatment. The reaction solution obtained in the         operation (2) was cooled to the room temperature. Each layer of         the reaction solution was separated and the separated chloroform         solution was added to anhydrous sodium sulfate for drying         overnight. The chloroform solution passed through an alkaline         alumina column. The chloroform was removed at 30-40° C. with a         rotary evaporator. Vacuum dry was performed overnight at 30° C.         with a vacuum of 2-3 kpa, wherein a resulting product is the         polymerizable surfactant with reducibility.     -   (4) NMR analysis of the product. A small amount of the product         was used for NMR analysis, and the solvent is deuterated         chloroform. The peak at the chemical shift δ=6.26 indicates two         H atoms on the double bond, the two triple peaks at the chemical         shift δ=4.29 and the chemical shift δ=4.15 respectively indicate         —CH₂— connected to the ester bond, δ=2.60 indicates —CH₂—         connected to N, δ=2.29 indicates two —CH₃ connected to N,         δ=1.2-1.7 indicates —CH₂— on the long alkyl group, δ=0.88         indicates —CH₃ on the end of the long alkyl group. FIG. 1 is an         exemplary nuclear magnetic resonance (NMR) image of         2-(dimethylamino)ethyl maleate dodecyl ester in embodiment 1.

Embodiment 2

-   -   (1) Preparation of an intermediate. 5.61 g (0.05 mol) itaconic         anhydride and 9.32 g (0.05 mol) lauryl alcohol were stirred at         80° C. for 1 h at the molten state. 15 ml heptane was added to         the molten mixture. The molten mixture was stirred to form a         uniform solution. The solution was placed for 3 h at room         temperature with stirring, and placed for 2 h at 15° C. with         stirring. A precipitate was collected. The precipitate was         recrystallized with heptane for 2-3 times. A solid was obtained         by filtration. The solid was washed with water for 2-3 times.         The intermediate monoester was obtained by freeze drying         overnight. The yield may reach 93.5%.     -   (2) Preparation of the polymerizable surfactant with         reducibility. 11.92 g (0.04 mol) itaconic acid monododecyl ester         was dissolved in 100 ml chloroform. A water solution of 11.06 g         (0.08 mol) potassium carbonate and 1.05 g (0.004 mol) 18-crown-6         was added dropwise to the chloroform solution at room         temperature. The mixture was stirred at 50° C. for 0.4 h. A         water solution of 5.76 g (0.04 mol) 2-dimethylamino chloroethane         hydrochloride (Aladdin, CAS: 4584-46-7) was added dropwise to         the above water-chloroform solution, for reaction at 50° C. for         20 h.     -   (3)The post-treatment. The reaction solution obtained in the         operation (2) was cooled to the room temperature. Each layer of         the reaction solution was separated. The separated chloroform         solution was added to anhydrous sodium sulfate for drying         overnight. The chloroform solution passed through an alkaline         alumina column. The chloroform was removed at 30-40° C. with a         rotary evaporator. Vacuum dry was performed overnight at 30° C.         with a vacuum of 2-3 kpa, wherein a resulting product is the         polymerizable surfactant with reducibility.     -   (4) NMR analysis of the product. A small amount of the product         was used for NMR analysis, and the solvent is deuterated         chloroform. The peaks at the chemical shift δ=6.34 and the         chemical shift δ=5.72 indicates two H atoms on the double bond,         δ=3.34 indicates —CH₂— connected to the carbonyl group, two         triple peaks at the chemical shift δ=4.27 and the chemical shift         δ=4.08 indicate —CH₂-connected to the ester bond. δ=2.60         indicates —CH₂— connected to N, δ=2.29 indicates —CH₃ connected         to N, δ=1.2-1.7 indicates —CH₂— on the long-chain alkyl, δ=0.88         indicates —CH₃ on the end of the long alkyl group. FIG. 2 is an         exemplary NMR image of itaconic acid 2-(dimethylamino)ethyl         dodecyl.

Embodiment 3

(1) Preparation of an intermediate. 4.90 g (0.05 mol) maleic anhydride and 11.79 g (0.055 mol) tetradecanol were stirred at 80° C. for 1 h at the molten state. 15 ml heptane was added to the molten mixture. The molten mixture was stirred to form a uniform solution. The solution was placed for 3 h at room temperature with stirring, and placed for 2 h at 15° C. with stirring. A precipitate was collected. The precipitate was recrystallized with heptane for 2-3 times. A solid was obtained by filtration. The solid was washed with water for 2-3 times. The intermediate monoester was obtained by freeze drying overhight. The yield may reach 91.5%.

-   -   (2) Preparation of the polymerizable surfactant with         reducibility. 12.48 g (0.04 mol) monotetradecyl maleate was         dissolved in 100 ml chloroform. A water solution of 11.06 g         (0.08 mol) potassium carbonate and 1.05 g (0.004 mol) 18-crown-6         was added dropwise to the chloroform solution at room         temperature. The mixture was stirred at 60° C. for 0.4 h. A         water solution of 5.76 g (0.04 mol) 2-dimethylamino chloroethane         hydrochloride (Aladdin, CAS: 4584-46-7) was added dropwise to         the above water-chloroform solution, for reaction at 50° C. for         20 h.     -   (3)The post-treatment. The reaction solution obtained in the         operation (2) was cooled to the room temperature. Each layer of         the reaction solution was separated. The separated chloroform         solution was added to anhydrous sodium sulfate for drying         overnight. The chloroform solution passed through an alkaline         alumina column. The chloroform was removed at 30-40° C. with a         rotary evaporator. Vacuum dry was performed overnight at 30° C.         with a vacuum of 2-3 kpa, wherein a resulting product is the         polymerizable surfactant with reducibility.

Embodiment 4

-   -   (1) Preparation of an intermediate. 5.61 g (0.05 mol) itaconic         anhydride and 10.72 g (0.05 mol) tetradecanol were stirred at         80° C. for 1 h at the molten state. 15 ml heptane was added to         the molten mixture. The molten mixture was stirred to form a         uniform solution. The solution was placed for 3 h at room         temperature with stirring, and placed for 2 h at 15° C. with         stirring. A precipitate was collected. The precipitate was         recrystallized with heptane for 2-3 times. A solid was obtained         by filtration. The solid was washed with water for 2-3 times.         The intermediate monoester was obtained by freeze drying         overnight. The yield may reach 92.5%.     -   (2) Preparation of the polymerizable surfactant with         reducibility: 13.04 g (0.04 mol) itaconic acid monotetradecyl         ester was dissolved in 100 ml chloroform. A water solution of         11.06 g (0.08 mol) potassium carbonate and 1.05 g (0.004 mol)         18-crown-6 was added dropwise to the chloroform solution at room         temperature. The mixture was stirred at 50° C. for 0.4 h. A         water solution of 5.76 g (0.04 mol) 2-dimethylamino chloroethane         hydrochloride (Aladdin, CAS: 4584-46-7) was added dropwise to         the above water-chloroform solution, for reaction at 50° C. for         20 h.     -   (3)The post-treatment. The reaction solution obtained in the         operation (2) was cooled to the room temperature. Each layer of         the reaction solution was separated. The separated chloroform         solution was added to anhydrous sodium sulfate for drying         overnight. The chloroform solution passed through an alkaline         alumina column. The chloroform was removed at 30-40° C. with a         rotary evaporator. Vacuum dry was performed overnight at 30° C.         with a vacuum of 2-3 kpa, wherein a resulting product is the         polymerizable surfactant with reducibility.

Embodiment 5

-   -   (1) Preparation of an intermediate. 4.90 g (0.05 mol) maleic         anhydride and 0.25 g (0.055 mol) lauryl alcohol were stirred at         80° C. for 1 h at the molten state. 15 ml heptane was added to         the molten mixture. The molten mixture was stirred to form a         uniform solution. The solution was placed for 3 h at room         temperature with stirring, and placed for 2 h at 15° C. with         stirring. A precipitate was collectedThe precipitate was         recrystallized with heptane for 2-3 times. A solid was obtained         by filtration. The solid was washed with water for 2-3 times.         The intermediate monoester was obtained by freeze drying         overnight. The yield may reach 91.3%.     -   (2) Preparation of the polymerizable surfactant with         reducibility. 11.36 g (0.04 mol) monododecyl maleate was         dissolved in 100 ml chloroform. A water solution of 11.06 g         (0.08 mol) potassium carbonate and 1.05 g (0.004 mol) 18-crown-6         was added dropwise to the chloroform solution at room         temperature. The mixture was stirred at 60° C. for 0.4 h. A         water solution of 6.32 g (0.04 mol) 3-(N, N-dimethyl)         amino-1-chloropropane hydrochloride (Aladdin, CAS: 5407-04-5)         was added dropwise to the above water-chloroform solution, for         reaction at 50° C. for 20 h.     -   (3)The post-treatment. The reaction solution obtained in the         operation (2) was cooled to the room temperature. Each layer of         the reaction solution was separated. The separated chloroform         solution was added to anhydrous sodium sulfate for drying         overnight. The chloroform solution passed through an alkaline         alumina column. The chloroform was removed at 30-40° C. with a         rotary evaporator. Vacuum dry was performed overnight at 30° C.         with a vacuum of 2-3 kpa, wherein a resulting product is the         polymerizable surfactant with reducibility.

Embodiment 6

-   -   (1) Preparation of an intermediate. 4.90 g (0.05 mol) maleic         anhydride and 10.25 g (0.055 mol) lauryl alcohol were stirred at         80° C. for 1 h at the molten state. 15 ml heptane was added to         the molten mixture. The molten mixture was stirred to form a         uniform solution. The solution was placed for 3 h at room         temperature with stirring, and placed for 2 h at 15° C. with         stirring. A precipitate was collected. The precipitate was         recrystallized with heptane for 2-3 times. A solid was obtained         by filtration. The solid was washed with water for 2-3 times.         The intermediate monoester was obtained by freeze drying         overnight. The yield may reach 92.8%.     -   (2) Preparation of the polymerizable surfactant with         reducibility. 11.36 g (0.04 mol) monododecyl maleate was         dissolved in 100 ml chloroform. A water solution of 11.06 g         (0.08 mol) potassium carbonate and 1.05 g (0.004 mol) 18-crown-6         was added dropwise to the chloroform solution. The mixture was         stirred at 60° C. for 0.4 h. A water solution of 6.88 g (0.04         mol) 3-dimethylamino-2-methyl-1-chloropropane hydrochloride         (Aladdin, CAS: 4261-67-0) was added dropwise to the above         water-chloroform solution, for reaction at 50° C. for 20 h.     -   (3)The post-treatment. The reaction solution obtained in the         operation (2) was cooled to the room temperature. Each layer of         the reaction solution was separated. The separated chloroform         solution was added to anhydrous sodium sulfate for drying         overnight. The chloroform solution passed through an alkaline         alumina column. The chloroform was removed at 30-40° C. with a         rotary evaporator. Vacuum dry was performed overnight at 30° C.         with a vacuum of 2-3 kpa, wherein a resulting product is the         polymerizable surfactant with reducibility.

Embodiment 7

Styrene (5.01 g, 0.0480 mol) was added to a reaction bottle including 2-(dimethylamino)ethyl maleate lauryl ester (0.3550 g, 0.0010 mol), sodium bicarbonate (0.15 g, 3 wt % styrene), potassium sulfate (0.1344 g, 0.0005 mol), and water (20.07 g, 400 wt % styrene). The solution was stirred evenly. After vacuuming and deoxygenating, the solution was placed at 25° C. for 8 hours to obtain a stable emulsion. The conversion rate of the styrene was 91.07%. The polymer was analyzed by triple-detection gel permeation chromatography and the results were as follows: M n.SEC=418000 g/mol, M w.SEC=2560000 g/mol, PDI=6.1.Mark-Houwink,α=0.6756, an average branching factor g′=0.66. The molecular weight distribution curve of the obtained polymer is in FIG. 3 .

Embodiment 8

Styrene (5.0005 g, 0.0480 mol) was added to a reaction bottle including itaconic acid 2-(dimethylamino)ethyl dodecyl (0.3552 g, 0.0010 mol), sodium bicarbonate (0.15 g, 3 wt % styrene), potassium sulfate (0.1340 g, 0.0005 mol), and water (20.07 g, 400 wt % styrene). The solution was stirred evenly. After vacuuming and deoxygenating, the solution was placed at 25° C. for 8 hours to obtain a stable emulsion. The conversion rate of the styrene was 98.05%. The polymer was analyzed by triple-detection gel permeation chromatography and the results were as follows: M n.SEC=263000 g/mol, M w.SEC=2970000 g/mol, PDI=11.3.Mark-Houwink, α=0.5992, an average branching factor g′=0.52.

Embodiment 9

Styrene (5.00 g, 0.0480 mol) was added to a reaction bottle including 3-(dimethylamino)propyl maleate lauryl ester (0.3555 g, 0.0010 mol), sodium bicarbonate (0.15 g, 3 wt % styrene), potassium sulfate (0.2619 g, 0.0010 mol), and water (20.07 g, 400 wt % styrene). The solution was stirred evenly. After vacuuming and deoxygenating, the solution was placed at 25° C. for 8 hours to obtain a stable emulsion. The conversion rate of the styrene was 90.25%. The polymer was analyzed by triple-detection gel permeation chromatography and the results were as follows: M n.SEC=530000 g/mol, M w.SEC=6520000 g/mol, PDI=12.3.Mark-Houwink, α=0.889, an average branching factor g′=0.50.

Comparative Example 1

Styrene (5.0006 g, 0.0480 mol) and N,N-dimethylaminoethyl methacrylate (0.1510 g, 0.0010 mol) was added to a reaction bottle including sodium bicarbonate (0.1500 g, 3 wt % styrene), potassium persulfate (0.2596 g, 0.0010 mol), and water (20.0020 g, 400 wt % styrene). The solution was stirred evenly. After vacuuming and deoxygenating, the solution was placed at 25° C. There is no reaction in the system. 

1. (canceled)
 2. A method for preparing a polymerizable surfactant with reducibility, wherein a general structural formula of the polymerizable surfactant with reducibility is represented as:

wherein a lonq-chain alkyl R₁ is —C₁₂H₂₅ or —C₁₄H₂₉, and a lonq-chain alkyl R₂ is —C₂H₄— or —C₃H₆—: the method comprising: performing a reaction based on an anhydride long-chain fatty alcohol, and hydrochloride of dimethylaminohaloalkane; and obtaining the polymerizable surfactant with reducibility through a post-treatment performed on a reaction solution obtained based on the reaction.
 3. (canceled)
 4. The method of claim 2, wherein an amount-of-substance ratio of the anhydride and the long chain fatty alcohol is 1:1 to 1.1.
 5. (canceled)
 6. (canceled)
 7. The method of claim 2, wherein the anhydride is itaconic anhydride.
 8. The method of claim 2, wherein the long-chain fatty alcohol is dodecanol or tetradecanol.
 9. The method of claim 2, wherein the hydrochloride of dimethylaminohaloalkane is 2-dimethylaminochloroethane hydrochloride, 3-(N, N-dimethyl) amino-1-chloropropane hydrochloride, or 3-dimethylamino-2-methyl-1-chloropropane hydrochloride.
 10. The method of claim 2, wherein performing the reaction based on the anhydride, the long-chain fatty alcohol, and the hydrochloride of dimethylaminohaloalkane includes: obtaining an intermediate of anhydride monoester by reacting the anhydride with the long-chain fatty alcohol; and obtaining the reaction solution by reacting the obtained intermediate with the hydrochloride of dimethylaminohaloalkane.
 11. The method of claim 10, wherein an amount-of-substance ratio of the hydrochloride of dimethylaminohaloalkane and the intermediate of anhydride monoester is 1 to 1.1:1.
 12. The method of claim 10, wherein obtaining the intermediate of anhydride monoester by reacting the anhydride with the long-chain fatty alcohol includes: mixing the anhydride and the long-chain fatty alcohol; heating the mixture of the anhydride and the long-chain fatty alcohol to a molten state; adding heptane to the molten mixture to form a solution; cooling the solution to obtain a precipitate; and obtaining the intermediate of anhydride monoester by recrystallization, filtration, washing, and freeze drying with respect to the precipitate.
 13. The method of claim 10, wherein obtaining the reaction solution by reacting the obtained intermediate with the hydrochloride of dimethylaminohaloalkane includes: dissolving the intermediate of anhydride monoester in chloroform; adding an aqueous solution of potassium carbonate and 18-crown-6 to the intermediate anhydride monoester chloroform solution; and obtaining the reaction solution by adding an aqueous solution of the hydrochloride of dimethylaminohaloalkane to the intermediate anhydride monoester chloroform solution for reaction.
 14. The method of claim 13, wherein an amount-of-substance ratio of the potassium carbonate, the 18-crown-6, and the intermediate of anhydride monoester is 2:0.1:1.
 15. The method of claim 10, wherein obtaining the intermediate of anhydride monoester by reacting the anhydride with the long-chain fatty alcohol includes: mixing the anhydride and the long-chain fatty alcohol; heating the mixture of the anhydride and the long-chain fatty alcohol to a molten state at 80° C.; stirring the molten mixture for 1 h; adding heptane to the molten mixture; stirring the molten mixture to form a uniform solution; stirring and cooling the solution to room temperature; placing the solution for 3 h; stirring and cooling the solution to 15° C.; placing the solution for 2 h; collecting a precipitate; recrystallizing the precipitate with heptane for 2-3 times; obtaining a solid by filtration; washing the solid with water for 2-3 times; and obtaining the intermediate of anhydride monoester by freeze drying.
 16. The method of claim 10, wherein obtaining the reaction solution by reacting the obtained intermediate with the hydrochloride of dimethylaminohaloalkane includes: dissolving the intermediate of anhydride monoester in chloroform; adding an aqueous solution of potassium carbonate and 18-crown-6 drop by drop to the intermediate anhydride monoester chloroform solution at room temperature; stirring the chloroform solution at 50-60° C. for 0.4 h; and obtaining the reaction solution by adding an aqueous solution of the hydrochloric of dimethylaminohaloalkane drop by drop to the intermediate anhydride monoester chloroform solution for reaction at 50° C. for 15-20 h.
 17. The method of claim 2, wherein obtaining the polymerizable surfactant with reducibility through the post-treatment performed on the reaction solution obtained based on the reaction includes: cooling the reaction solution to room temperature; separating each layer of the reaction solution; adding separated chloroform solution to anhydrous sodium sulfate for drying; passing the chloroform solution through an alkaline alumina column; removing the chloroform; and performing vacuum dry, wherein a resulting product is the polymerizable surfactant with reducibility.
 18. The method of claim 2, wherein obtaining the polymerizable surfactant with reducibility through the post-treatment performed on the reaction solution obtained based on the reaction includes: cooling the reaction solution to room temperature; separating each layer of the reaction solution; adding separated chloroform solution to anhydrous sodium sulfate for drying overnight; passing the chloroform solution through an alkaline alumina column; removing the chloroform at 30-40° C. with a rotary evaporator; performing vacuum dry overnight at 30° C. with a vacuum of 2-3 kpa, wherein a resulting product is the polymerizable surfactant with reducibility. 